Abstract
An Antarctic coral belonging to the order Pennatulacea, collected during the 2013 austral autumn by trawl from 662 to 944 m depth, has yielded three new briarane diterpenes, bathyptilone A-C (1–3) along with a trinorditerpene, enbepeanone A (4), which bears a new carbon skeleton. Structure elucidation was facilitated by one- and two-dimensional NMR spectroscopy, mass spectrometry and confirmed by X-ray crystallography. The three compounds were screened in four cancer cell lines. Bathyptilone A displayed selective nanomolar cytotoxicity against the neurogenic mammalian cell line Ntera-2.
Highlights
Since the late 1950s, marine organisms have been increasingly important as sources of novel secondary metabolites, many of which demonstrate significant biological activity
More than 90% of the ocean exists at temperatures below 3 ◦ C, yet only 2% of natural products are reported from marine organisms collected in these regions [1,2], reflecting, in part, that such environments remain difficult to access
We describe the isolation and structure elucidation of two classes of compounds isolated from an Antarctic specimen of Anthoptilum grandiflorum, including (Scheme 1) briaranes, bathyptilone A–C (1–3) and the new scaffold of a trinorditerpene, enbepeanone A (4), likely derived from a briarane precursor
Summary
Since the late 1950s, marine organisms have been increasingly important as sources of novel secondary metabolites, many of which demonstrate significant biological activity. Briarane diterpenes were first described four decades ago and the ensuing years have seen more than 600 reported in the literature [11]. They exhibited a wide range of biological activities, including cytotoxicity, anti-inflammatory, antiviral, insecticidal and immunomodulatory activity [12,13,14,15,16]. We describe the isolation and structure elucidation of two classes of compounds isolated from an Antarctic specimen of Anthoptilum grandiflorum, including (Scheme 1) briaranes, bathyptilone A–C (1–3) and the new scaffold of a trinorditerpene, enbepeanone A (4), likely derived from a briarane precursor.
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